Alkoxide-promoted [1, 3] rearrangements of 1, 3-dithianes

…, RN Misra, GM Georgiadis

Index: Wilson, Stephen R.; Misra, Raj N.; Georgiadis, Gregory M. Journal of Organic Chemistry, 1980 , vol. 45, # 12 p. 2460 - 2468

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Citation Number: 18

Abstract

The allylic alcohols formed from 1, 2-addition of 2-lithio-1, 3-dithianes to a,@-unsaturated ketones have been shown to undergo [1, 3] rearrangement to afford their respective Michael- addition products upon treatment with KH in HMPA/THF in some cases. The major side reaction and in some instances the sole reaction pathway was fragmentation. The rearrangement was applied to a two-carbon macrocyclic ring-expansion strategy which is ...